After over a year of not travelling, what better way to ease into the fun of sightseeing than a short weekend getaway?! City breaks are a wonderful way to experience a refreshing change in scenery, and this trip was no exception. If you want to find out how to make the most of a weekend in Chicago, keep reading!
The L-train (short for elevated) is a cheap and convenient way to get around the city, without the hassle of getting stuck in traffic. Day passes can easily be purchased at stations, and trains are fairly frequent too. Rideshare apps like Uber and Lyft are also a good option if you want the convenience of a car, without the faff of trying to find a nearby parking spot.
Start off your trip with a birds eye of Chicago from the top of Willis tower (formerly Sears tower). This is a very popular spot, so make sure to arrive early to beat the crowds. A short, but swift elevator takes you to the top. From there, you will be able to walk around and take in 360 degree views of the city.
Chicago River Walk
Right by the river is a path stretching a little over a mile long, which is a great place to stroll around and enjoy the cool breeze. Many restaurants line the river walk, making this a great spot for lunch.
Fun fact: While it is popular believed that Chicago is called the ‘windy city’ not because of the cold winds blowing off of Lake Michigan, there is also the belief that the nickname originates from Chicago politicians being ‘windbags’ who would talk your ears off and were full of hot air!
Architecture River Cruise
By this point, you certainly will have noticed the plethora of beautiful sky scrapers all around town. You can learn more about the vast architectural history of the city while enjoying a relaxing cruise down the river. There are multiple tour operators on the river, with multiple departures throughout the day. We took one by Wendella, and had a great experience with them.
The Millenium park is home to Cloud gate, more colloquially known as the Bean. If you don’t have a picture of this, did you even visit Chicago?! Since it is a very popular spot, don’t expect to get a photo without anyone else in it unless you go really early in the morning or late at night. During the day, it is a great place to people watch or relax outdoors if the weather is good. Make sure you walk underneath to enjoy the sculpture to enjoy the reflections!
Chicago Art Institute
Close to Millenium park is the Art Institute of Chicago, which is one of the oldest art museums in the world. Their collection includes the works of Monet, Van Gogh, Salvadore Dali, Picasso and O’Keefe among many others. Easily recognizable from the bronze lion statues guarding the entrance, it is definitely worth stopping in for if you can.
Try a Deep dish Pizza
Chicago is synonymous with deep dish pizza, and what better way to end a packed day of sightseeing? Giordano’s pizza, who have multiple locations across Chicago, was suggested to us by multiple people, and it did not disappoint. Note that because they are freshly baked, it takes 45 mins for your food to come out. It is also extremely popular, so be prepared for a long wait or order it to go.
One of the absolute highlights during our trip was our visit to the Field Museum. The museum is most famous for Sue, the largest and most complete T-Rex fossil ever found, which is absolutely worth seeing. However that is not all, as the museum has a large number of amazing exhibits at any time. I would highly recommend scheduling more time than you think you will need, as there is just so much to see.
Grab a Chicago Style Hot Dog
If you are feeling a little peckish after all that walking around, this is a perfect time to grab yourself a Chicago style hot dog. These are topped with onions, relish, yellow mustard and a pickle spear. One thing that you will NOT find on it is ketchup. Most of the hot dog stands that we came across also had vegan hot dogs, which was amazing to see!
Shedd Aquarium / Adler Planetarium
Also on Museum campus along with the Field museum are the Shedd aquarium and the Adler planetarium, which are a short walk away from each other. Covering all three attractions will take more than one day, so depending on how long you are spending in Chicago and your personal preference, pick one of the two to visit. (Note: The planetarium is closed in 2021 due to the pandemic).
Wander down the Magnificent Mile
If you are in the mood for some retail therapy, or simply want to take in the city, walk down the ‘Magnificent Mile’ or the ‘Mag Mile’ for short. This 13 block stretch is full of shops, restaurants and hotels, so you are sure to find something that piques your interest.
Tips and Tricks
If you plan on visiting multiple attractions during your visit, consider getting the Chicago city pass. The pass allows access to 5 attractions for a flat rate, and as a bonus you also get to skip the line at a number of the attractions. Check out the pass here.
If you are short on time, try to find a hotel in the Loop area to make the most of your weekend in Chicago. We stayed at the Central Loop hotel, and it was very convenient to walk to most of the attractions listed here. If you’re really looking to splurge, The Langham is a highly rated option.